She agrees to give it a shot

“O... okay!”

“What was that?!”

“Okay!” she repeated, still incredulous what she heard her own voice say. She was agreeing to let a colleague fuck her in the ass! “But if I say stop, we stop!”

“Naturally!” Jacobs nodded, fighting back a huge grin with moderate success as he watched her hesitantly pull away her hand, once more giving him a good view of her asshole. Reaching into his pocket, he pulled out a small bottle of lube.

“Hmm?!” Nancy watched with a bit of amusement mixing into her anxiety. “Well, look who is prepared. Confident, aren’t we?!”

He shrugged. “Better have it and don’t need it than need it and don’t have it…” Popping the cap, he squeezed a healthy amount of the translucent gel into his palm, already warmed by his body temperature after he had carried it in his pocket. “And you are going to love it, trust me! Spread your ass cheeks!”

Nancy blushed at how matter-of-factly he ordered her something so lewd. Embarrassed, she closed her eyes and turned her head away, unable to look at him as she meekly obeyed. Her fingers dug into the honed musculature of her buttocks and she pried them apart. An audible whimper of humiliation escaped her lips as her mind couldn’t help but focus on how sluttily she acted.

On the other hand, Jacobs savored the moment, enjoying the submissive view of how Nancy presented herself, her embarrassment causing his cock to harden a little more. Loving that she couldn’t even bear to look at him, he took his time before he reached down and gently applied a deliberate amount of the gel to her sphincter, rubbing it around the wrinkled rim. The sounds she made as he took his time to massage it into every small nook and cranny were amazing. Pathetic, humiliated whimpering mixed with slutty, pleasurable moans as she predictably loved it. He was careful not to push her too hard too soon and he had her purring once again with carnal joy when he finally proceeded. Nancy gave a guttural, decidedly unladylike grunt as his finger pushed in, taking a significant amount of lube with it. At this point he had worked her enough so he was easily able to penetrate, but her sphincter was still incredibly snug, grabbing his finger in a tight, vice-like embrace. Nonetheless, she responded perfectly, bucking back against his hand as he began to fingerfuck her asshole, spreading the viscous gel inside her rectum while simultaneously working to loosen her tense muscles.

Soon he was able to add a second finger, eliciting a cute little squeal and her dainty toes wriggled adorably before her groans became even deeper, the primal pleasure reducing Nancy to her most feral responses. He smirked, seeing her twat dripping wet. From his first day at the office where she had strutted around like a superstar he had known she’d love it in the ass and now he was proven right! Two fingers up the backdoor and she was literally creaming herself.

He took his time, gradually increasing the pace and only twice briefly stopping to add more lube, but eventually his hand was working her hard and fast, easily sliding in and out of her well-lubed asshole. Nancy had completely forgotten herself, face deep red and shamelessly crying her pleasure out into the alley. He wasn’t sure if there were any apartments in the vicinity, but if there were, the inhabitants were getting an earful.

He made sure to have her on the brink of loosing her mind when he suddenly stopped, forcing his fingers as deep as he could and stopping there. Nancy gasped, her small feet kicking the air, her mind completely blown.

Jacobs grinned. Leaning in, he planted a soft kiss on her warm, quivering buttock. “What is going to happen next, Nancy?” he asked.

She gave off a throaty, helpless moan. He could tell she wasn’t entirely there, her mind dissolving in a rampant party of endorphins, but a curling, massaging motion deep inside her butthole made her obey. “Y-you’re going to fuck my ass!” she groaned. Her voice was slurred, half-muffled by the couch’s leather cushion, delirious.

“Exactly!” Jacobs nodded with a satisfied smirk. “Stay like this! Don’t move a muscle!”

Nancy whined when he slowly retracted his fingers from her asshole, but she did as she was told, keeping her cheeks spread wide. As his digits slid out her sphincter twitched, pulling tight for a second before it relaxed again, stretched into a small, oval gape by her own hands.

His eyes fixed on the submissive bitch in front of him, Jacobs stood up. He squeezed another portion of lube straight onto his shaft before tossing the bottle onto the couch next to Nancy as he rubbed it all over his cock. He continued to take his time and let her wait, knowing every second would feel like **** to her.